“Jackie was very consumed with getting him on the right path,” Simon wrote of the Kennedy mother and son. It’s not difficult to figure out what it was about the Queen of Pop that Jackie took umbrage with. The fact of their opposing personalities aside, Jackie couldn’t have loved Madge’s sartorial allusions to Marilyn Monroe (with whom the late JFK was rumored to have carried on an affair). But what reportedly really upset Jackie was the singer’s inclusion of crosses and other religious iconography in her aesthetic. (Jackie was raised Catholic.)

Though she bore strong opinions about her son’s love life, it was Jackie’s own romances that puzzled the public, particularly her marriage to Greek shipping magnate Aristotle Onassis. “She said he was very sexy — he would sing to her on his yacht and take her great places to make love,” Simon wrote of the surprising couple. “She knew marrying him was the bad-girl move. In a way I never knew whether she was sticking up for her own decision or whether she really loved him.”